Hydrogen–deuterium exchange of aromatic amines and amides using deuterated trifluoroacetic acid. Issue 5 (28th January 2015)

• Record Type: Journal Article
• Authors: Giles, Richard; Lee, Amy; Jung, Erica; Kang, Aaron; Jung, Kyung Woon
• Is Part Of: Tetrahedron letters. Volume 56:Issue 5(2015)
• Page Start: 747
• Page End: 749
• Publication Date: 2015-01-28
• Subjects: H–D exchange -- CF3COOD -- Acetaminophen -- Electrophilic aromatic substitution -- Brønsted acid; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2014.12.102
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The H–D exchange of aromatic amines and amides, including pharmaceutically relevant compounds such as acetaminophen and diclofenac, was investigated using CF3 COOD as both the sole reaction solvent and source of deuterium label. The described method is amenable to efficient deuterium incorporation for a wide variety of substrates possessing both electron-donating and electron-withdrawing substituents. Best results were seen with less basic anilines and highly activated acetanilides, reflecting the likelihood of different mechanistic pathways.